Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Crossdressing For Fun

Personal Stories, Advice, and Support 745 People

    Pleasure Perfect

    I have been a cross dresser from a very young age. In puberty and ever since it has been a huge sexual turn on for me. I used to dress up as often as possible and still do. It always gets me excited to the point, when I was younger I had to relieve myself. Now that I'm older I...
    zymack zymack 56-60, M 5 Responses Mar 9, 2012

    Your Response

    Cancel

    First Time In Front Of Friends

    Like some boys and men, I have tried cross-dressing on occasion. As a teenager, I would get sexually aroused by it. I would wear (let's say a girl's swimsuit), look at myself in the mirror and try to imagine a girl in that certain outfit and that would excite me. These occasions...
    LittleMelissa LittleMelissa 61-65, M 21 Responses Apr 6, 2012

    Your Response

    Cancel

    Started Late

    I was raised in a family environment that was pretty straight and church going. If I had desires out of the norm, they were thoroughly suppressed. As an adult, I worked in a very macho world, any display of feminine characteristics would have caused serious repercussions for me...
    Pat398 Pat398 56-60 1 Response Jul 14, 2012

    Your Response

    Cancel

    Crossdressing..it's Not Just A Hobby Anymore

    From our first meeting my wife knew I found being smooth and hairless (save for a pink puff above my erect clitty)and attired in satin and nylon and silky feeling attire to be a turn on I was driven to. From my early teens on, the fetish to visually assume (and eventually...
    CYNDIMC CYNDIMC 31-35 3 Responses Sep 23, 2012

    Your Response

    Cancel

    Waiting To Dress Up

    I live in a boarding home now I like to dress up in private and can`t do it here I have not had a bra or panties on in about a year 1/2. I dream of it really. last night in a dream my wife was measuring me for a bra.
    crosserJonie crosserJonie 51-55, M May 23, 2012

    Your Response

    Cancel

    Deeper Than The Fun

    living fulltime as a female now, taking natural hormones to change my body, and planning on having srs, but i still love dressing like a woman every single day. the fun part for me is showing off my inner female in public. people for the most part take me for a genetic female...
    Mizsuzy Mizsuzy 46-50, T 2 Responses May 2, 2012

    Your Response

    Cancel

    First Time In Front Of Friends...(adding To It)

    I was in a dream state sitting at my friends' dinning room table. It was my alone time, as my friends were preparing dinner in the kitchen. I was a princess waiting to be served by my two friends. My dress was a powder blue and a style very similar to what Princess Diana (bless...
    LittleMelissa LittleMelissa 61-65, M 3 Responses Apr 9, 2012

    Your Response

    Cancel

    Happiness...

    It is a happy time, those moments or those days where I am free to dress in my "good" clothes. There is a relaxation to shedding the jeans and tee in trade for the blouse and skirt one that hasn't been experienced in any other situation. Now then, I am a straight, married male...
    DonnaSt DonnaSt 66-70, M 6 Responses Jul 14, 2012

    Your Response

    Cancel

    Crossdresser From Time To Time.

    There's times that I don't wear any women's clothes with the exception of pantyhose or ocassionally some women's shorts. But there are times that everyday I just have the big urge to slip into a blouse and a skirt and some women's shoes and a wig. It just feels so great to dress...
    montserrat70 montserrat70 41-45, M 1 Response Mar 10, 2013

    Your Response

    Cancel

    My Wife's Nighties

    I enjoy wearing my wife's nighties when she is not around, as it gets me in the right mood for when she comes home. The feeling of the material rubbing against my bare flesh is a real turn on. I have a couple of favourite nighties that i always go for, but tonight i went for...
    toril34 toril34 51-55, M 2 Responses Jul 20, 2012

    Your Response

    Cancel

    For The Fun

    I started fully cross-dressing when I was about 23yrs old after wearing just tights/pantyhose from about13/14, I think it is rather nice to cross-dress for the fun of it as there is a wider range of items you can wear when you are cross-dressing as a woman.
    xdpaul xdpaul 56-60, M Jun 22, 2012

    Your Response

    Cancel

    Love To Crossdress

    I think of crossdressing all the time. Wearing panties, lingerie, pantyhose, stockings, skirts, and other womans clothing is always on my mind. Crossdressing just makes me feel so alive, happy, calm, relaxed and always puts me in a good mood, as well as making me more excited...
    pantiescouple pantiescouple 26-30 2 Responses Feb 17, 2012

    Your Response

    Cancel

    Relaxing

    I find crossdressing fun. It is the only time of the day where I can relax. It is simple and easy for me. I have a favorite outfit to wear, panties, bra, and silk nightie. Just having that material on is worth putting in the time.
    sharonlynne sharonlynne 41-45, M 3 Responses Jan 22, 2013

    Your Response

    Cancel

    I Love Crossdressing

    I crossdress because it is fun, it feels good, it is highly erotic and I have the best ******* I have ever had. I love looking at photos of beautiful Ladyboys while I am dressed in very sensual sexy outfits, pantyhose and high heels and make love to myself while imagining making...
    candiceldubonet candiceldubonet 46-50, T Apr 21, 2012

    Your Response

    Cancel

    Me Too

    I wear all dresses of women. ... But I don't want to be feminine. I wear them only just for fun and pleasure.
    lingarielover lingarielover 31-35, M 2 Responses Apr 12, 2012

    Your Response

    Cancel

    Related Experiences

    Hi i am a female still in middle school and i want to crossdress.But how can i hide it? i mean from my elders and maybe classmates...but anyways it would not be hard for me to fit...
    crosdreser123 crosdreser123 18-21, F 1 Response 5 days ago

    Your Response

    Cancel
    I my using my sexy gf for fun and love
    xhmkq8 xhmkq8 13-15, M 4 days ago

    Your Response

    Cancel
    I do this sometimes when there is no one else here. Its relaxing. I have about 7 pairs now. A tall plain black pair, a union jack pair, a cow print pair, Peter Stormare's multi...
    Ganner Ganner 22-25, M Jul 2

    Your Response

    Cancel
    Dancing is one of the things that I greatly enjoy. It is a fun thing to do too!
    DamoiseauDynavolt DamoiseauDynavolt 16-17, M 1 Response Jul 6

    Your Response

    Cancel
    I'm dragging you funny people in a net.... Your my prisoners...
    eatthekids1stplease eatthekids1stplease 18-21, M Jul 17

    Your Response

    Cancel
    I'm here to have fun and express things I might not in real life. I don't plan to ever meet anyone in person or have serious conversations if you want that there are plenty of...
    checkingin123 checkingin123 26-30, M 6 days ago

    Your Response

    Cancel
    My 5 year old video =D www.youtube.com/watch?v=gtIV3w-Oqmk
    umerqazi umerqazi 22-25, M 2 Responses Jun 30

    Your Response

    Cancel
    Some people just dont care, if they want something they will take it, then throw it away when it no longer suites them!! I really despize that behaviour and wouldnt wish the...
    strikeslucky strikeslucky 51-55, M Jul 1

    Your Response

    Cancel
    I live in Montreal, hit me up ;)
    ThatGuyMTL ThatGuyMTL 16-17, M 1 Response a week ago

    Your Response

    Cancel
    Dang, school definitely sucks.... No social life :(
    JessiLin JessiLin 16-17, F 6 days ago

    Your Response

    Cancel
    I love to see sexy young girls that are into older men and that i like to ****
    wildbillbigcock wildbillbigcock 31-35, M 1 day ago

    Your Response

    Cancel
    In my opinion, being funny is a must. you have to make me laugh cause I love laughing . I just fall quickly for funny guys. if you can make my stomach hurt laughing , I love you.
    xriiccii xriiccii 13-15, F 1 day ago

    Your Response

    Cancel
    I'm looking for fun (and cheap) things to do with my girlfriend. Maybe some date ideas or just things to do together at home (besides the obvious lol). Any ideas, guys?
    DeadHeretic DeadHeretic 26-30, M Jul 8

    Your Response

    Cancel
    I'm looking for fun (and cheap) things to do with my girlfriend. Maybe some date ideas or just things to do together at home (besides the obvious lol). Any ideas, guys?
    DeadHeretic DeadHeretic 26-30, M 1 Response Jul 8

    Your Response

    Cancel
    This happened when I was in fifth grade. A couple minutes before we were called in from recess, I came across a ball, the type normally used for games like kickball (for those who...
    BLACKTIGER75 BLACKTIGER75 36-40, M 1 Response Jul 10

    Your Response

    Cancel
    On Jan 3, 2013 I had shared a story on EP and it was simply about how it is so hard for some to find that right connection and be part of someones life, and be together either...
    Shinesaathlove Shinesaathlove 46-50, M 2 Responses Jul 14

    Your Response

    Cancel
    I have nothing against religious people or atheists. To me they are both the same. Just people with beliefs. They can be good or bad depending on their personality. Beliefs can...
    Ultimatedorktroid Ultimatedorktroid 16-17, F Jul 2

    Your Response

    Cancel
    I was at my sisters house at the time and I forgot to take off my green with pink dotted thong and she saw it over my jeans waist and she took all my underwear away and said if I...
    Pantyhoseboy1 Pantyhoseboy1 18-21, M 1 Response 13 hrs ago

    Your Response

    Cancel
    Sometimes people think that crossdressing automatically would make someone seem gay, but that isn't it! Crossdressing is just a thing that some men (or women) like to do! It makes...
    naco26withcheese naco26withcheese 13-15, M 1 Response Jul 19

    Your Response

    Cancel
    Personally I think we all need one, it's always great to have some fun and be great friends and comfortable with that person be it via the Internet and just chatting sending pics...
    69morninglory69 69morninglory69 26-30, M 8 mins ago

    Your Response

    Cancel
    One of the biggest issues we have in life is that people tend to care a lot more than they should about others opinion. Like just because someone thinks different than you doesn't...
    PeaceAtSoul PeaceAtSoul 16-17, T 2 Responses 10 hrs ago

    Your Response

    Cancel
    I haven't slept since yesterday.. I had a lot to do and there was no time to sleep, so I just took a good coffee and had some pain killers with caffeine later.. I'm awake but I'm...
    ThePeach ThePeach 26-30, F 6 hrs ago

    Your Response

    Cancel
    So today, i got PE class and so I was wearing a shirt, jogging pants and my running shoes. To be honest, i dont really look good with that.. I look like a potato. Well i am a...
    kmisfit123 kmisfit123 16-17, F 2 Responses 4 hrs ago

    Your Response

    Cancel
    My whole family attended the 70th bday party of our neighbor and its full of old people in our community ballroom dancing . You know like dance partners are already ready and if...
    trentoy trentoy 18-21, M 1 Response 1 hr ago

    Your Response

    Cancel
    The first time i was caught crossdressing i wad 16 and wearing high heals, fish net stockings, a short skirt, a small skimpy shirt and makeup on. The worst part is my mom caught me...
    bottomslut1 bottomslut1 18-21, M 2 Responses Jul 6

    Your Response

    Cancel
    Why are females who accept a guys feminine side so hard to find? Looking to chat to females or males who accept crossdressing 💋
    susspender susspender 41-45, M 4 Responses Jul 12

    Your Response

    Cancel
    When I was 12 i realised a loved the feel of female clothing being a guy myself it was strange I knew my mum would freak if she found my out so in the end i decided to make my own...
    Crossdresserman Crossdresserman 22-25, M 4 Responses Jul 13

    Your Response

    Cancel
    I have been crossdressing since I was in my teens .over the years the compulsion to dress as a woman has intensified dramatically .i now dress completely with full make up and am...
    francescalewis1956 francescalewis1956 56-60, M 1 Response 6 days ago

    Your Response

    Cancel
    I tried out for my first time ever a dress, heels, and wig! I had no idea heels are so addicting, I only want more lol. Never had I thought dressing up all girly other than...
    VeryImportantPerson VeryImportantPerson 26-30, M 1 Response Jul 2

    Your Response

    Cancel
    Looking for some one to share story's about getting caught wearing girls panties or crossdressing
    ddavis21 ddavis21 18-21, M 1 Response Jul 13

    Your Response

    Cancel
    Hey, so I'm waiting for someone special I already know who it is. Him and I have been childhood friends till I moved away when I was 8. We went and did everything together because...
    EvelynElf EvelynElf 16-17, F 1 Response 6 hrs ago

    Your Response

    Cancel
    I was a lost girl. I was trying to find myself. That was until I met someone online last summer. We became really good friends, talked about life and played around. We promised...
    JumpingTomatoes JumpingTomatoes 16-17 7 Responses 7 hrs ago

    Your Response

    Cancel
    Saw a vid with this in it thought it was funny... So ya...
    doubletimeit doubletimeit 18-21, M 1 hr ago

    Your Response

    Cancel
    I've often thought about this and what I would actually cook for them. Of course, you have to take into account allergies, intolerances, any diets and likes and dislikes. I don't...